Réaction #10827

Équation de réaction

hydrazine

2,4-dimethoxy-benzoic acid methyl ester

→

2,4-dimethoxy-benzoic acid hydrazide

Rendement 78.1%

Solvants

methanol

Conditions de réaction

Traitement

1. 1
   AutreSolvent was removed under reduced pressure
2. 2
   workup.DISSOLUTIONThe residue was re-dissolved in ethyl acetate
3. 3
   LavageThe solution of ethyl acetate was washed with saturated solution of sodium bicarbonate and brine
4. 4
   Séchagedried over sodium carbonate
5. 5
   Concentrationconcentrated

Mode opératoire

Ex-109A: A solution of 2,4-dimethoxy-benzoic acid methyl ester (4.24 g, 21.6 mmol) and hydrazine (3.4 mL, 108.1 mmol) in methanol (50 mL) was refluxed overnight. Solvent was removed under reduced pressure. The residue was re-dissolved in ethyl acetate. The solution of ethyl acetate was washed with saturated solution of sodium bicarbonate and brine, dried over sodium carbonate and concentrated to afford 2,4-dimethoxy-benzoic acid hydrazide (3.31 g, 78%) as a white solid: 1H NMR (CDCl3) δ 8.77 (bs, 1H), 8.15 (d, J=8.8 Hz, 1H), 6.58 (dd, J=8.8, 2.2 Hz, 1H), 6.46 (d, J=2.2 Hz, 1H), 4.10 (bs, 2H), 3.91 (s, 3H), 3.83 (s, 3H).

Source